Island institution The Club Car got an upgrade under new ownership, with a remodel to its iconic railway car interior and the addition of a considerably more elevated menu than the Club Car of yore (actually: No one really came here to eat.) Now, find California-inspired, locally sourced, seasonal shared plates from executive chef Mayumi Hattori. Rest assured, the bar-restaurant’s famous live piano and delightfully surly bartenders remain.

Thursday nights throughout the summer, the Nantucket Hotel’s Grand Ballroom takes guests back in time for an evening of “refined sophistication” in the form of fine dining, quiet conversation, live jazz, ballroom dancing. (Think more Moet & Chandon, less tequila and beer backs.) Executive chef Bill Weisse’s three-course menu features American classics and dress is “island elegant:” boas and pearls for the ladies; jackets and ties for the gents. A concurrent Kids Club means you can drop the littles for activities and a movie and collect them after you’ve waltzed your last waltz.

Sister restaurant to Galley Beach and neighbor to Greydon House, subterranean seafood bistro and wine bar Afterhouse isn’t just another fish joint. Billed as a speakeasy, there’s no phone, no reservations (but there are lines, so get there early). The wait is worth it, though, for small plates that include just-dug oysters (with creative sauces like cilantro-Thai and miso yogurt), ceviche and the like, perhaps the largest selection of tinned seafood in New England, and, of course, caviar. Doors open at 2:30 and close when the party’s over.

The 20-room hotel on the cobblestoned corner of Broad and North Water is a design lover’s dream, a renovated 1850s Greek Revival with custom interiors and furnishings by Roman and Williams that include bespoke beds and Portuguese maritime murals (there’s also a signature scent developed by Cinnamon Projects). Dark wood accents and flame-stitch upholstery are a welcome reprieve from all the whitewashed beadboard and whale décor around town, while creating an especially cozy vibe for off-season. The cocktail menu was curated by Jackson Cannon, one of Boston’s top mixologists, and though the bar is stunning, hands down one of the hotel’s best features is the roving cocktail cart that travels room-to-room pre-dinner.

A few doors down from Greydon House is Lark Hotels’s 21 Broad, housed in one of the island’s oldest properties, a 27-room Victorian with a front porch built for reading (and people watching). The inside, however, is totally modern: Jonathan Adler accents, iPads for use during your stay, and a nightly BYOB mixer bar with juices, bitters, garnishes, and more. There’s no in-house restaurant —just breakfast—but that’s okay: You’re right in the heart of town (even the Steamship ferry is in walking distance).

Expect secluded beaches, magnificent sunsets, and massages so good you'll spend the last 15 minutes obsessing over how to fit in another. On the quiet northern side of the island, the resort caters to a more refined weekend away: private cottages, fewer crazy crowds (virtually no crazy co-eds), top notch dining with a practically clairvoyant sommelier, sunsets by the fire pit, bikes to borrow, and a complimentary water taxi to check in on the throngs downtown, if you feel you must.

The newest addition to the White Elephant family, the village offers rooms in the modern main inn as well as two- and three-bedroom residences featuring all the comforts of home. But the real showpiece is the swimming pool and cabanas, where the hotel has thought of everything: complimentary magazines and books, sunglass cleaner, SPFs of all scents and numbers, and (hooray!) mimosas all day long. There are also BMW courtesy cars for in-town drop-off, complimentary bicycles to use for the beach or for a trip to town, and a lobby display of complimentary snacks and drinks, like cheese, pastries, cookies, coffee and tea, and fresh fruit water.

The island’s local beer maker and distillery—and the country’s first outdoor brewery—plays host to a crossroads of islanders, and their dogs, in a laid-back, picnic-tabled setting with live music, a tented raw bar, corn hole, and play areas for kids. There’s a variety of Cisco beer on tap, including Island Reserve, a double IPA available only on island, as well as cocktails made with vodka, whiskey, rum, and gin from the adjacent Triple Eight Distillery (you can also buy a refillable growler for brews-to-go). Catch the free shuttle from in town or drive or bike yourself there.

Executive chef Liam Mackey dishes up interesting, innovative, and super-tasty dishes from land and sea with influences from Hawaii, Thailand, Indonesia, and beyond. Try the crispy fried Brussels sprouts with Vietnamese fish sauce, tempura East Coast oyster tacos wrapped in nori, Berkshire pork buns, and the famous blue crab fried rice. Cocktails build on the theme, using house made syrups, tinctures, and bitters; standouts include the Teach Me How to Dougie, featuring crema mezcal, grapefruit, and ginger and the When in Rome, a white Negroni made with gin and Lillet. There’s also Fernet on tap! Show up in person at noon to snag a same-day reservation, or call starting at 1 and prepare to beg.

An island institution among the white jeans and navy cardigan set, the Galley offers some of the only on-sand drinking on the island, with an extensive list of rosés—still the island’s unofficial wine of choice—and hands down one of the very best sunset views on island. You’ll pay a bit extra for the privilege, perhaps—a $40-something glass of wine here is not unusual, and there’s one for $129. (But the view!)

The hotel’s stunning views of Nantucket bay are made even more stunning at sunset, of which the deck at Topper’s offers the island’s most magical view. There’s also, of course, the food. Everyone’s doing poke these days, and the Hamachi version here doesn’t disappoint. Also guaranteed-to-please: the Panzanella salad; the Block Island swordfish; the cooked-to-perfection Pineland Farms N.Y. Strip. The wine list is dizzying, but even if you know your stuff, take our advice: Let Craig choose what you’ll be drinking. And for dessert, the fresh-baked cookies are famous and, really, fresh-baked. Expect to wait 20 minutes for your plate of three—go straight up chocolate chip—all of them entirely worth it.

Overlooking Nantucket Harbor, the patio offers classic New England views… but chances are, you’ll spend all your time people watching instead. Expect an eclectic mix of guests, all of them tanned and well dressed. Cozy up at one of the patio tables or dine inside for a more elegant vibe (until the tabletop dancing starts, that is). The order, obviously, is seafood: The smoked fish dip will change your life. The lobster cocktail (with fennel and kumquat) is so fresh it was swimming that morning. If you’re not a seafood fan, the chicken under a brick is delicious. Cocktails-wise, have a Beachside (or five) on us. Tell them we sent you. Thank us later.

An island institution for more than 50 years, The Chicken Box is where you go for your dive fix (locals call it “the Box”). Don’t expect pristine (or even clean floors)—never mind rosé. This is a tequila and Bud Light sort of place. Live music is some of the best in town, but don’t get there before 10 p.m. or everyone will know it’s your first time here.

If your idea of a great brunch is the one that lasts for hours, and on island time it should, Millie’s has all the makings of perfection: strong and spicy Bloody Marys, panoramic ocean views, a lawn made for letting the kids run wild, and the sort of food you’ve been craving since the night before.

Pick a spot on the front lawn and order up the house best: scallop tacos, lobster quesadillas, grilled Mexican corn, and the Altar Rock, a life-changing salsa, guacamole, and cheese dip. And some Bloody Marys. Lots of Bloody Marys.

Hamptons wine heiress Joey Wolffer’s “roving boutique” pops up in Nantucket every summer offering new and vintage clothing and accessories finds from around the world, as well as bags of her own design. Find boho dresses well-suited for sunset cocktails, and cold-shoulder tops that’ll serve you well while getting down at the Chicken Box.

The Boston-based fitness brand is all about the subtle art of workout wear. That doesn’t mean fashion falls by the wayside: In addition to a white-gray-blue color palette that never goes out of style, Crane & Lion’s leggings, tanks, and wrap tops offer details like color-blocking and hints of mesh, and enough versatility to take you from barre to the bar. There’s something here to flatter nearly every body (even if you’ve lately been doing more bar than barre). Don’t expect animal print anything. Deal with it—you’re on Nantucket.

An eco-minded beauty boutique with an expansive selection of skincare, hair care, and cosmetics from more than 30 made-in-the-USA brands. Owner Tara Foley will happily guide you in the right direction to exactly what you’re looking for. We left with a tub of Organic Bath Co.’s addicting Refreshmint Scrub and our skin has never been smoother (or mintier!). Also, Soapwalla’s Deodorant Cream, which Tara swore by, and we have to agree: Our days of drugstore deodorant have officially been numbered.

Owner Courtney McKechnie’s spacious apparatus-based Pilates studio (with ample parking out front) deals in beach-perfect bodies, with classically-trained instructors leading private, semi-private, and small group classes designed to get you toned and back on the beach in the shortest amount of time possible. Challenging, sweat inducing, and best of all, effective. Forgot your workout gear? Not a worry. McKechnie loves fashion almost as much as she loves fitness and she stocks an array of flattering, hard to find pieces from OmGirl, Beyond Yoga, Lululemon, Testament, and more.

A beautifully curated selection of home accessories, furniture, and barware guaranteed to bring a colorful punch to your beach house (or a splash of summer to your primary house). Need a hostess gift? Here’s the go-to for picking up a last-minute candle or sea-inspired present, including baby alpaca throws, handmade oak whale cutting boards, personalized cocktail napkins, and more.

Owner Elisabeth English has a beyond-amazing collection of vintage clothing: racks upon racks of vintage Lilly Pulitzer (for women and men), Lanz, Malia of Honolulu and more, including, come fall, an epic selection of fur-trimmed coats. Staffers are skilled in guiding guests to items that would fit well, knowing it can be tough to find a vintage ensemble that actually works for your body. All that and wine! And lots of it: currentVintage also stocks a selection of wine and champagne.

A great excuse to “forget your bathing suit” at home. Shop the beautiful selection of Eres swimwear, Roberta Roller Rabbit cover-ups, and easy dresses that can take you from the beach to dinner. And for the needlework aficionado: Expect kits of all shapes and sorts.

What you’ll covet: Everything. This adorable little bohemian shop imports the most luminous black pearls from Tahiti and sells them, it would seem, to the most elegant ladies in town. Our favorite: The Julia necklace. One single stunning pearl on an adjustable cord.

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